ES2303672T3 - Analogos piperidinilos de la prostaglandina e. - Google Patents
Analogos piperidinilos de la prostaglandina e. Download PDFInfo
- Publication number
- ES2303672T3 ES2303672T3 ES05705822T ES05705822T ES2303672T3 ES 2303672 T3 ES2303672 T3 ES 2303672T3 ES 05705822 T ES05705822 T ES 05705822T ES 05705822 T ES05705822 T ES 05705822T ES 2303672 T3 ES2303672 T3 ES 2303672T3
- Authority
- ES
- Spain
- Prior art keywords
- oxo
- piperidin
- acid
- phenyl
- acetic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 PIPERIDINYL Chemical class 0.000 title claims description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 148
- 150000004702 methyl esters Chemical class 0.000 claims description 75
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 18
- 208000010412 Glaucoma Diseases 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 206010030043 Ocular hypertension Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UEQLULDETPANRS-WNWYLPOESA-N 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetamide Chemical compound C1CCC(=O)N(CCCCOCC(=O)N)[C@H]1\C=C\C(O)CC1=CC=CC(Cl)=C1 UEQLULDETPANRS-WNWYLPOESA-N 0.000 claims description 3
- PDOUDCKFVFFXHP-WNWYLPOESA-N 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound C(\[C@@H]1N(C(=O)CCC1)CCCCOCC(O)=O)=C/C(O)CC1=CC=CC(Cl)=C1 PDOUDCKFVFFXHP-WNWYLPOESA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000002997 ophthalmic solution Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- OHTBRSPZGKGPNX-WBVIWABJSA-N 2-[(z)-4-[(2r)-2-(3-hydroxy-4-phenylbutyl)-6-oxopiperidin-1-yl]but-2-enoxy]acetic acid Chemical compound C=1C=CC=CC=1CC(O)CC[C@H]1CCCC(=O)N1C\C=C/COCC(O)=O OHTBRSPZGKGPNX-WBVIWABJSA-N 0.000 claims 2
- RPKGGMKLCKYHFQ-PYTPGESOSA-N 2-[(z)-4-[(6r)-2-oxo-6-(3-oxo-4-phenylbutyl)piperidin-1-yl]but-2-enoxy]acetic acid Chemical compound C1CCC(=O)N(C\C=C/COCC(=O)O)[C@H]1CCC(=O)CC1=CC=CC=C1 RPKGGMKLCKYHFQ-PYTPGESOSA-N 0.000 claims 2
- PJHOQCPGTGEHBS-MRTLOADZSA-N 2-[4-[(2r)-2-(3-hydroxy-4-phenylbutyl)-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound C=1C=CC=CC=1CC(O)CC[C@H]1CCCC(=O)N1CCCCOCC(O)=O PJHOQCPGTGEHBS-MRTLOADZSA-N 0.000 claims 2
- TXBOLWFTFXGCJQ-HRYKLGGKSA-N 2-[4-[(2r)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound C(\[C@@H]1N(C(=O)CCC1)CCCCOCC(O)=O)=C/C(O)CC1=CC=CC=C1 TXBOLWFTFXGCJQ-HRYKLGGKSA-N 0.000 claims 2
- AHYHCKDKOKOYEC-GOSISDBHSA-N 2-[4-[(6r)-2-oxo-6-(3-oxo-4-phenylbutyl)piperidin-1-yl]butoxy]acetic acid Chemical compound C1CCC(=O)N(CCCCOCC(=O)O)[C@H]1CCC(=O)CC1=CC=CC=C1 AHYHCKDKOKOYEC-GOSISDBHSA-N 0.000 claims 2
- QEIDWGFEZPFPRO-IENJSVCTSA-N 2-[4-[(6r)-2-oxo-6-[(e)-3-oxo-4-phenylbut-1-enyl]piperidin-1-yl]butoxy]acetic acid Chemical compound C1CCC(=O)N(CCCCOCC(=O)O)[C@H]1\C=C\C(=O)CC1=CC=CC=C1 QEIDWGFEZPFPRO-IENJSVCTSA-N 0.000 claims 2
- 229940054534 ophthalmic solution Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- 238000000746 purification Methods 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000003818 flash chromatography Methods 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- 239000007832 Na2SO4 Substances 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 14
- 125000004494 ethyl ester group Chemical group 0.000 description 13
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 13
- 150000003180 prostaglandins Chemical class 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000012267 brine Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 229960002986 dinoprostone Drugs 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- IMERILGFAXLHDH-YGPZHTELSA-N (6r)-6-(1-ethoxyethoxymethyl)piperidin-2-one Chemical compound CCOC(C)OC[C@H]1CCCC(=O)N1 IMERILGFAXLHDH-YGPZHTELSA-N 0.000 description 4
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 108010008655 Epstein-Barr Virus Nuclear Antigens Proteins 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
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- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000001077 hypotensive effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
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- VIXWNAKNIOPREN-UHFFFAOYSA-N (2-oxo-3-phenylpropyl)phosphonic acid Chemical compound OP(O)(=O)CC(=O)CC1=CC=CC=C1 VIXWNAKNIOPREN-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- GLLKTTGKUHEZBJ-SNVBAGLBSA-N 2-[4-[(2r)-2-(hydroxymethyl)-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound OC[C@H]1CCCC(=O)N1CCCCOCC(O)=O GLLKTTGKUHEZBJ-SNVBAGLBSA-N 0.000 description 2
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- 238000003653 radioligand binding assay Methods 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VMOQVTPKGUXWKA-RXMQYKEDSA-N (6r)-6-(hydroxymethyl)piperidin-2-one Chemical compound OC[C@H]1CCCC(=O)N1 VMOQVTPKGUXWKA-RXMQYKEDSA-N 0.000 description 1
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/763,702 US6977260B2 (en) | 2004-01-22 | 2004-01-22 | Piperidinyl prostaglandin E analogs |
| US763702 | 2004-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2303672T3 true ES2303672T3 (es) | 2008-08-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05705822T Expired - Lifetime ES2303672T3 (es) | 2004-01-22 | 2005-01-14 | Analogos piperidinilos de la prostaglandina e. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6977260B2 (enExample) |
| EP (1) | EP1722795B1 (enExample) |
| JP (1) | JP4740883B2 (enExample) |
| AR (1) | AR047436A1 (enExample) |
| AT (1) | ATE394101T1 (enExample) |
| AU (1) | AU2005209209B2 (enExample) |
| CA (1) | CA2553387C (enExample) |
| DE (1) | DE602005006534D1 (enExample) |
| ES (1) | ES2303672T3 (enExample) |
| TW (1) | TWI348370B (enExample) |
| WO (1) | WO2005072735A1 (enExample) |
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| US7326716B2 (en) * | 2003-06-06 | 2008-02-05 | Allergan, Inc. | Treatment of inflammatory bowel disease |
| WO2006047466A2 (en) * | 2004-10-21 | 2006-05-04 | Duke University | Ophthamological drugs |
| US20070254920A1 (en) * | 2006-04-26 | 2007-11-01 | Aerie Pharmaceuticals, Inc. | Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3220156C2 (de) * | 1982-05-28 | 1990-01-25 | Heida Houston Tex. Thurlow | Mit Metallgriffen, insbesondere Edelstahlgriffen, versehenes Koch- und Bratgeschirr mit Deckel |
| IT1225716B (it) * | 1988-10-26 | 1990-11-22 | Esacontrol Spa | Dispositivo per la protezione dei rele' di binario dai disturbi elettrici |
| CA2021316C (en) | 1989-07-27 | 2000-10-24 | Ming Fai Chan | Intraocular pressure reducing 11-acyl prostaglandins |
| US5034413A (en) | 1989-07-27 | 1991-07-23 | Allergan, Inc. | Intraocular pressure reducing 9,11-diacyl prostaglandins |
| US4994274A (en) | 1989-07-27 | 1991-02-19 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins and method of using |
| US5028624A (en) | 1989-07-27 | 1991-07-02 | Allergan, Inc. | Intraocular pressure reducing 9,15-diacyl prostaglandins |
| DE4318713C1 (de) * | 1993-06-07 | 1994-09-15 | Daimler Benz Ag | Zahnräderwechselgetriebe der Vorgelegebauart |
| JP4766875B2 (ja) * | 2002-06-06 | 2011-09-07 | メルク フロスト カナダ リミテツド | Ｅｐ４受容体作動薬、組成物及びその方法 |
| US7053085B2 (en) | 2003-03-26 | 2006-05-30 | Merck & Co. Inc. | EP4 receptor agonist, compositions and methods thereof |
| WO2004063158A1 (en) | 2003-01-10 | 2004-07-29 | F.Hoffmann-La Roche Ag | 2-piperidone derivatives as prostaglandin agonists |
| US6747037B1 (en) * | 2003-06-06 | 2004-06-08 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| WO2004108215A1 (en) * | 2003-06-06 | 2004-12-16 | Allergan, Inc. | Piperidinyl prostaglandin e analogs |
-
2004
- 2004-01-22 US US10/763,702 patent/US6977260B2/en not_active Expired - Lifetime
-
2005
- 2005-01-07 TW TW094100542A patent/TWI348370B/zh not_active IP Right Cessation
- 2005-01-14 DE DE602005006534T patent/DE602005006534D1/de not_active Expired - Lifetime
- 2005-01-14 CA CA2553387A patent/CA2553387C/en not_active Expired - Fee Related
- 2005-01-14 ES ES05705822T patent/ES2303672T3/es not_active Expired - Lifetime
- 2005-01-14 EP EP05705822A patent/EP1722795B1/en not_active Expired - Lifetime
- 2005-01-14 AT AT05705822T patent/ATE394101T1/de not_active IP Right Cessation
- 2005-01-14 WO PCT/US2005/001461 patent/WO2005072735A1/en not_active Ceased
- 2005-01-14 AU AU2005209209A patent/AU2005209209B2/en not_active Ceased
- 2005-01-14 JP JP2006551189A patent/JP4740883B2/ja not_active Expired - Fee Related
- 2005-01-20 AR ARP050100195A patent/AR047436A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE394101T1 (de) | 2008-05-15 |
| HK1099203A1 (en) | 2007-08-10 |
| AU2005209209B2 (en) | 2012-03-08 |
| EP1722795A1 (en) | 2006-11-22 |
| AU2005209209A1 (en) | 2005-08-11 |
| WO2005072735A1 (en) | 2005-08-11 |
| US6977260B2 (en) | 2005-12-20 |
| TWI348370B (en) | 2011-09-11 |
| CA2553387A1 (en) | 2005-08-11 |
| TW200533350A (en) | 2005-10-16 |
| EP1722795B1 (en) | 2008-05-07 |
| AR047436A1 (es) | 2006-01-18 |
| US20050164990A1 (en) | 2005-07-28 |
| JP2007520489A (ja) | 2007-07-26 |
| JP4740883B2 (ja) | 2011-08-03 |
| DE602005006534D1 (de) | 2008-06-19 |
| CA2553387C (en) | 2013-04-02 |
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